


Cherry Whiskey Jubilee

by troubleseeker



Series: kinktober 2018 [11]
Category: Supernatural
Genre: Anal Sex, Bottom Sam, Dark, Dean Winchester in Denial, Drag, Drunk Sex, Drunkenness, Hurt, Other, Panties, Sam in Makeup, Sam in a dress, Top Dean, Wincest - Freeform, bra - Freeform, but Dean has no idea, cross-dressing, no comfort, safe sex
Language: English
Status: Completed
Published: 2018-10-11
Updated: 2018-10-11
Packaged: 2019-07-29 14:04:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,688
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16265723
Author URL: https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker
Summary: kinktober day 11 - Object Insertion | Sounding |Cross-dressing |Tribadism/ScissoringDean gets absolutely hammered on cheep whiskey, and can't believe his luck when a gorgeous,tall girl in a pretty dress steps into his dark broody room and asks him for a kiss. Alcohol and hormones make it all go down heavy, but Dean is in denial about who he's with.





	Cherry Whiskey Jubilee

**Author's Note:**

> Dean is drunk, which could introduce elements of dub-con. He thinks he's with a girl. No one is underage when it comes to the sex bit ... the drinking ... well ...

God she looked hot. Hair down and curling around her ears, lips so plush and soft he couldn’t help but kiss them. 

“Sorry m’drunk.” He apologised. Whiskey soaked lips pressing against hers again anyway.

“Don’t care.”

Dean hummed. Already thanking his lucky stars she found her way into  _ his _ motel room. She was perfect. Taller than he was, but he wasn’t so shallow to care about that. Dean winchester was man enough to stand on his tiptoes to kiss a girl. And she leaned down to kiss him back, so they were meeting right in the middle. 

He licked at her lips, asking nicely to be let in, because she was too precious to go rough with. 

Shy yet willing, she parted her lips. And God he wanted more. Hands in her hair, he drew her in. Down. Guiding her to sit on the bed. She bounced a bit on the shoddy mattress, looking up at him through lashes sloppily laden with mascara. Bringing every ounce of bravado to the surface, Dean let his bow legs corral hers. Tipped her face up with one finger under her chin for a near chaste kiss, before he took another swig of whiskey.

“Never done this before, darling?”

She shook her head, bangs falling across her face and hiding her face. Made her look even nicer. Still, she took a sip when he offered the bottle - small and dainty - the rim came back stained with lipstick.

Taking his time, telegraphing his moves, Dean placed first one then his other knee on the bed. Straddling her lap and kissing her good and proper. 

Inexperienced, she tried to copy his - frankly advanced - moves.

Dean smoothed a hand down the pale blue dress. He didn’t know what the material was, but it was soft, and it shimmered in the light. Not that there was all that much light inside the room at all. Whiskey tasted best in the dark, and he hadn’t bothered turning it back on again after she walked in.

“Don’t worry.” He cooed. Abandoning her mouth to nip at her ears. Tugging the clip on earrings off to nibble at the sensitive lobes underneath. “I’ll take care of you.” 

Just as Dean knew she would, the girl gasped and grabbed hold of his shoulders to steady herself. Some things never changed. He’d been with a ton of girls. Been honing his skills since they were interested, really. And they all gasped and went all soft when he bit in the right places. 

Like right behind the ear. First a fingertip, then his tongue, then his teeth.

The girl shivered, gasped, then moaned. Hands going tighter. Big hands.

And that had to be a plus, because no tiny girl had hands like that. She could probably take his whole dick in just one of them if she wanted to jack him off. Dean had to bite back a moan of his own. Maybe later.

With a girl as sweet as this one he’d have to be a perfect gentleman, and that meant that the girl came first. … in every way.

One hand in her hair - God it was soft - they went back to kissing, and emboldened by her eagerness Dean let his free hand wander lower. 

Smooth skin on her neck, dipping into a sweetheart neckline. Not too much breast to work with, but girls came in all shapes and sizes and as long as they were happy to get felt up by Dean, he was happy to do the feeling. 

He cupped what he could, fingers finding her nipples easily enough in turn. She gasped each time. Surprised by how good it felt. The look on her face truly astonished, and not played.

Dean often felt sad for sheltered girls, completely unaware of how good everything could be if they just let go. It did let him rock their worlds though. Resident bad boy who showed you the pleasure palace your body was, and then moved on. On to the next town, and its overabundance of girls who needed an outlet.

“Ever felt this good, darling?”

She groaned out the no as his hand made its way further south. 

“Wanna feel even better?”

Breathy little yeah, yeah, yeahs helped Dean guide her down onto the bed. Hair fanning out around her face, strong jaw smoothed out in the low light, and he stroked down blushing powdered cheeks as he slid off the bed and sank to his knees in between hers.

Dean’s hands started down low, gently holding on to her ankles and sliding slowly upwards. She had to be a runner or maybe a swimmer with legs like those. And Jesus Christ they just kept going. Trembling knees led into tense thighs that eventually relaxed as he massaged them. 

She was wearing pantyhose, wrapping her legs up all tight and dainty. Silky under his fingertips, catching on the rough edges in his skin. Unable to resist, he rubbed his head against them, five o’clock shadow rasping against the delicate material even as his hands sought the heat further up. Still covered by the skirt of the dress, Dean pushed till he could see sweet little panties. 

Grinning like the cat that got the cream, he took another big swig of booze. Lacy and white with small red cherries. They couldn’t be more appropriate, really. 

Licking and biting, he ventured higher and higher. The whiskey in his gut nowhere near as hot as the v of her legs. Smoothing his hands up her hips, down around her ass, he pulled the pantyhose down.

Definitely a runner. Ass plump and firm in a way he knew well. There was a reason guys went after cheerleaders. Not that he said no to any other girl, really. If Dean Winchester was anything, he wasn’t picky. 

Didn’t even care when he found furry legs. Nothing wrong with shaved legs. Nothing wrong with girls who didn’t see the point. He took the time to kiss one tense calf, just to show her how perfect she was. 

And then he was moving up again. Locking eyes with her - head raised to watch him - he surged up to lick a long stripe across the front of her panties. Raising the open bottle of Jack once more, before offering it to her as well.

She might be new at this, but she was courageous. He laughed. 

“You know how to party?”

Accepting the bottle, she nodded, taking a more sedate sip and grimacing at the burn. Dean grinned. She hadn’t been partying for too long.

“Pretty thing like you, must’ve been beating the other guys off you with a stick.” She laughed, a giggled thing that made her thighs shake under his hands. “But you saved yourself for me, didn’t you?”

She went still, staring deep into his alcohol clouded eyes before nodding. Free hand carding through his hair with more tenderness than he’d felt in a long time. 

Brain slipping sideways, Dean looked back down at the panties. He licked at them again, making the white go just a bit translucent. And then further down, fingers feeling the wetness before he saw it.

“You wet for me already, babygirl?”

She nodded, mumbling something under her breath. Shy again.

Dean knew what to do with that. 

“Scoot up a bit, babe.”

She obeyed, wriggling backwards and hiking up her skirt again, hips propped up for him to slide a finger underneath the panties to find her hole glistening.

“Shit, that’s so hot.”

Tongue itching, Dean surged forward to trail it up along the wet trail.

“Fuck, you kinky thing. Got yourself ready before you came in, didn’t you?”

She tasted of cherries. Saccharine sweet and fruity on the back of his tongue. Pulling her panties further to the side, Dean got his face closer. Swirling his tongue around the edge of her entrance before pressing deeper in. She reached down to help, pulling the sweet cherry print fabric clear of his objective. 

Hands free, he reached right up to pinch her nipples again.

“Gonna get out of that dress, doll?”

Blush too fevered to be contained by her makeup, she sat up and wriggled out of the frilly blue number. A dopey smile made its way onto Dean’s face. She sat above him, hands crossed demurely across her chest to half-hide the darling little bra cinched tight around her chest. 

It matched her panties. White, bit of lace, cute cherries scattered all over it. What was that thing people said? If her bra and panties match, you’re not the one who decided to have sex? Yeah. She’d thought this through. Not even including the lube. 

Thinking ahead. Probably had condoms in that tiny purse thing. Hot.

“Let me see, sweetheart.”

Biting at her glossy lips, she relented. Dropping her hands into her lap and then moving them to the bed. Exposed for him to gaze up at.

“You’re beautiful.”

She looked a bit sad, but smiled anyway.

“Really?”

Dean nodded, fingering her nipples through way less material. They hardened, more visible now through the thin cotton. The flush reached her chest.

“Yeah. Lie back down?”

Licking her lips, she did. Pushing further up the bed by shimying her hips. Letting him crawl up after her, let him get get comfy in between her legs. Whiskey still on his tongue, Dean needed more of that cherry goodness. Needed his tongue deep, and her voice high and wavering.

He took his time. Licking nibbling. Getting fingers within the deep heat of her body and reveling in the ease with which he was allowed in. She was active in keeping her hole nice and available. Pulling at her panties and his hair, mewling in delight. 

“Fuck, babe. You have no idea how bad I wanna get in there.”

Using his hair, she pulled him closer still; one palm pressing down on her clit. Grinding against his face while she tried to find her words

“Want_ ah_ want you to.”

Eyes barely peeking above her mound - he didn’t look at it too much, more interested in what her hands were doing - he tracked the condoms she pulled out of the dinky purse. A whole string of them. Crisp and new. Tearing the first one off and passing it down.

“Want you to fuck me. Please.”

Dean was pretty sure he’d never gotten his dick out this fast before. Jeans down around his ankles and his underwear following right after. She was getting just that tad more naked too, rolling over and pushing her panties down off her ass. 

Dean couldn’t resist going back for yet another lick of slick cherries. They were addictive. He finished with a last long lick, and a longer swig of whiskey.

“Want me to take you from behind, sweetheart?”

“Please.”

Muffled by the pillow but still plenty of consent. Dean rolled the condom onto his dick. Practised strokes as he eyed his target. Perfect cherry red bullseye.

“Always aim to please.” He hummed to himself, knee-walking onto the bed and watching her spread her cheeks. Showing him where his tongue had been … where his dick was going to go.

“Tell me if it hurts.” He slurred. “First time means I have to go slower than the porn you’ve been watching.”

Cause she had to have watched some good shit with the way she was behaving. 

Reminding himself to go  _ slow _ , Dean pressed in. And holy shit. He’d had some virgins in his time, but she was like a vice. Tight heat he pushed through till his brain was on fire. 

It took him ages to get all the way in, and yeah, it was a good thing she’d brought extra lube. 

“So tight, baby girl.”

All the way in now, Dean had the brainpower to look down at the quivering mess he’d shoved his dick into. Head turned to the side, make-up smeared all over the pillow, teary eyed.

“Shit. I hurt you?”

She shook her head. Licking her lips and scrubbing a hand across her face.

“No. ‘sjust intense.” 

Aah. That he could understand. 

“Alright. You tell me when you’re ready for more.”

And shit, he wanted to move. Wanted to grind ever deeper into her lythe body and never ever come back out. Wanted to move. Grab her hips and make sure she was never this tight for anyone else again.

Thoughts not actions, though. Dean stayed still. Rubbing soothing circles on her back and ass till she moved her hips on her own accord.

“Yeah?”

“Please?”

So fucking polite. Hands curling around her hips, Dean moved. Slowly at first - even going back to drizzle more sweet slick over his cock to make sure he did this the right way - but speeding up as she got used to the feeling. Bis brain was on fire. The breathy moans he punched out oh her with his cock were going to drive him insane.

“So good, babe. So good.”

God damn.

Time flies when you’re having fun. Flies even faster when you’re twenty-two and balls deep in one of the tightest pussies you’ve ever encountered. Dean thanked the lord that he was smashed. Alcohol helping him avoid shooting  _ too  _ early.

In the end, he managed to ride her long enough for her to reach underneath herself to get herself off. 

Under normal circumstances, Dean’d be doing that himself. But Christ, he was losing his mind over the vice around his cock and had no brain power left to move his hands further than her hips or waist.

There was no surviving her orgasm. Whatever he’d done to get her loose enough for him to fuck, slammed back tight as the first second he’d gotten up in her. Walls clenching around him, dragging his own orgasm out him whether he was good’n ready or not.

Too well trained in the art of stealth fucking to give in to the compulsion to scream, Dean folded double over the girl’s back with a harsh breath. Nose in her hair as he pumped the condom full of juice. Boneless as all the energy drained from his body.

He barely managed to remember the condom. Grabbing it at the base of his dick as he rolled off of her. 

Really, the cold air on his spent cock was the saddest thing he’d felt in ages. Early twenties or not, there was no way he’d be getting it back up for another round. Cursing, he pulled off the rubber and tied it off. Finding the near empty bottle of booze when he tossed it somewhere near-ish to the trash can. 

“You c’n stay if you want.” He slurred, lips already back around the bottle to forget about the perfection he’d just fucked. They’d move on soon. Better forget it ever happened. He’d find another tall girl in another tiny town. 

Sleep caught him before he knew her answer.

\---------------------------------------------------------------------------------------------------------------------------

The next morning, Dean woke clutching a frilly blue dress. Blinking hard, he found the panties and bra he’d dreamed about neatly laid out on the second bed. It was still neatly made ... hadn’t been slept in. Bathroom door open and dark. 

Dean groaned when he sat up straight-er; squinting angrily at the empty bottle on the nightstand. Had Sam not come home again? Bitch had been prissy for days.

“Shower.” He croaked to the empty room, pausing to sift through the stuff on Sam’s bed. What kind of girl just left behind their clothes and purse?

Next to the purse, the panties, and the bra he barely spotted the slip of paper. Torn hastily from a notebook. Maybe she’d had an emergency of some kind? HAd to sneak out at night and decided to go naked?

Wiping a hand down his face in an effort to wake up his eyes, Dean unfolded the ragged page. Instantly recognizing the handwriting. He’d known it since he’d coached the kid after school. Taking the time to watch him scrawl out the alphabet in big clunky letters.

 

_ I’m sorry I can’t be what you want, Dean. Thanks for trying, but I understand. I got into Princeton. _

_ Love you _

_ Sam. _

**Author's Note:**

> If you want to come yell at me on [tumblr](http://ryugarika.tumblr.com/) ... feel free to, I can take it.
> 
> Comments feed me!
> 
> Check back tomorrow, for ... licking, pet Play, Rimming, and costumes!! (Yes, all 4 ... I am a gluton for punishment) The sun is shining bright again, with some crack and fluff on the horizon.


End file.
